Find Deals on Flights from Caribbean to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Caribbean to Chicago

(Round-trip)
Depart: Tue Aug 29 2017 Return: Wed Aug 30 2017 Trip spans 2 days
American Airlines
American Airlines
KIN
ORD
8h 56m
1 stop
ORD
KIN
12h 40m
2 stops
Depart: Fri Apr 28 2017 Return: Sun May 7 2017 Trip spans 10 days
United
United
NAS
ORD
22h 53m
2 stops
ORD
NAS
3h 29m
nonstop
Depart: Fri Apr 28 2017 Return: Wed May 3 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
19h 29m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Wed Jul 12 2017 Return: Mon Jul 17 2017 Trip spans 6 days
Delta
Delta
NAS
MDW
12h 13m
1 stop
MDW
NAS
15h 30m
1 stop
Depart: Tue Apr 18 2017 Return: Tue May 30 2017 Trip spans 43 days
JetBlue
JetBlue
BQN
ORD
20h 47m
1 stop
ORD
BQN
19h 00m
1 stop
Depart: Tue Jun 13 2017 Return: Mon Jun 19 2017 Trip spans 7 days
Air Canada
Air Canada
POS
ORD
18h 48m
2 stops
ORD
POS
17h 40m
1 stop
Depart: Tue Apr 18 2017 Return: Tue May 2 2017 Trip spans 15 days
Major Airline
Major Airline
KIN
ORD
15h 20m
1 stop
ORD
KIN
10h 40m
1 stop
Depart: Thu Jul 27 2017 Return: Mon Jul 31 2017 Trip spans 5 days
Frontier
Frontier
PUJ
ORD
5h 10m
nonstop
ORD
PUJ
4h 47m
nonstop
Depart: Tue May 23 2017 Return: Sat Jun 10 2017 Trip spans 19 days
United
United
NAS
ORD
10h 52m
3 stops
ORD
NAS
3h 25m
nonstop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Tue May 9 2017 Return: Tue May 23 2017 Trip spans 15 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 42m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Thu Apr 20 2017 Return: Mon Apr 24 2017 Trip spans 5 days
American Airlines
American Airlines
PUJ
ORD
19h 00m
1 stop
ORD
PUJ
18h 32m
1 stop
Depart: Tue Apr 11 2017 Return: Sun Apr 16 2017 Trip spans 6 days
United
United
PUJ
ORD
5h 05m
nonstop
ORD
PUJ
4h 40m
nonstop
Depart: Thu May 11 2017 Return: Tue May 16 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
7h 38m
1 stop
MDW
SJU
13h 44m
2 stops
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 39m
1 stop
ORD
SJU
6h 55m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
JetBlue
JetBlue
NAS
ORD
8h 42m
1 stop
ORD
NAS
10h 04m
1 stop
Depart: Sat Sep 30 2017 Return: Wed Oct 4 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 27m
1 stop
MDW
SJU
13h 53m
2 stops
Depart: Sat Sep 23 2017 Return: Sun Oct 1 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 36m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 27 2017 Trip spans 26 days
United
United
NAS
ORD
28h 53m
2 stops
ORD
NAS
6h 45m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Aguadilla
$377
Nassau
$303
San Juan
$327
Kingston
$218
Punta Cana
$353
Piarco
$378
Destination

Chicago
only $218
only $366
Airlines Airline reviews

8 travelers who booked a flight from Kingston to Chicago rated their chosen airlines with an average of 6.8.

Overall
8.3
Boarding
7.2
Crew
8.3
Comfort
8.0
Food
7.3
Entertainment
7.5